Deoxyvasicinone with Anti-Melanogenic Activity from Marine-Derived Streptomyces sp. CNQ-617

Abstract

The tricyclic quinazoline alkaloid deoxyvasicinone (DOV, 1) was isolated from a marine-derived Streptomyces sp. CNQ-617, and its anti-melanogenic effects were investigated. Deoxyvasicinone was shown to decrease the melanin content of B16F10 and MNT-1 cells that have been stimulated by α-melanocyte-stimulating hormone (α-MSH). In addition, microscopic images of the cells showed that deoxyvasicinone attenuated melanocyte activation. Although, deoxyvasicinone did not directly inhibit tyrosinase (TYR) enzymatic activity, real-time PCR showed that it inhibited the mRNA expression of TYR, tyrosinase-related protein 1 (TRP-1), and tyrosinase-related protein 2 (TRP-2). In the artificial 3D pigmented skin model MelanodermTM, deoxyvasicinone brightened the skin significantly, as confirmed by histological examination. In conclusion, this study demonstrated that the marine microbial natural product deoxyvascinone has an anti-melanogenic effect through downregulation of melanogenic enzymes.

In Vitro Antioxidant and Antiaging Activities of Collagen and Its Hydrolysate from Mackerel Scad Skin (Decapterus macarellus)

“…The inhibition of tyrosinase activity is the focus of most techniques for reducing melanin formation. Tyrosinase is an enzyme that accelerates the pigmentation process by converting L-tyrosine to L-3,4-dihydroxyphenylalanine (L-DOPA), and, finally, dopaquinone, resulting in a polymerization reaction that produces melanin [ 12 ]. Despite the fact that melanin is a vital molecule for humans, excessive melanin production in the epidermis can lead to major dermatological issues, such as lentigines, melasma, and hyperpigmentation related to skin aging.…”

Thioquinoline derivatives conjugated to thiosemicarbazide as potent tyrosinase inhibitors with anti-melanogenesis properties

“…Melanin is a group of biopolymer pigments that is a mixture of dark brown or black eumelanin and lighter-colored pheomelanin in many organisms 1 . In humans, it protects the skin from UV radiation and other environmental challenges and gives the skin it's color 2 , 3 . However, the excessive accumulation of melanin might result in some disorders, such as melanoma, melasma, and freckles as well as increase the risk of cancer 4 , 5 and Parkinson's disease 6 .…”

One-Pot Synthesis of Isoxazole-Fused Tricyclic Quinazoline Alkaloid Derivatives via Intramolecular Cycloaddition of Propargyl-Substituted Methyl Azaarenes under Metal-Free Conditions

“…Quinazolinones are a well-known family of N -heterocyclic compounds with bioactivities [ 1 , 2 , 3 , 4 , 5 , 6 ] on multiple fronts and occur often in natural products [ 7 , 8 , 9 , 10 ]. Recently, a group of special tricyclic quinazoline alkaloids, such as 2,3-dihydropyrrolo[2,1- b ]quinazolin-9(1 H )-ones, have attracted increased attention from medicinal chemists and biologists for their bioactivity levels in areas such as antitumor, antibacterial, anti-inflammatory and anti-acetylcholinesterase activities [ 11 , 12 , 13 , 14 , 15 , 16 ]. Key examples include deoxyvasicinone and vasicinone isolated from the adhatoda vasica medicinal plant, with pronounced anti-inflammatory, antimicrobial, and antidepressant activities ( Figure 1 ) [ 17 , 18 , 19 , 20 ].…”